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Acta Pharm.

53 (2003) 7381

Original research paper

Analysis of the essential oils of the leaves, stems, rhizomes


and roots of the medicinal plant Alpinia galanga from
southern India

LEOPOLD JIROVETZ1*
GERHARD BUCHBAUER1
MOHAMED POTTACHOLA SHAFI2
NEETTIYATH KALATHIL LEELA3

The essential oils of the leaves, stems, rhizomes and


roots of the medicinal plant Alpinia galanga from southern India were investigated by GC-FID, GC-MS and olfactometry. In all four samples, mono- and sesquiterpenes
1 Institute of Pharmaceutical Chemistry
as well as (E)-methyl cinnamate could be identified.
They are responsible for the characteristic odor as well
University of Vienna
as for the reported use in (folk) medicine and in food
A-1090 Vienna, Austria
products of A. galanga.
2 Department of Chemistry
The essential oil of A. galanga leaves is rich in 1,8-cineole
Calicut University, Kerala 673 635, India (28.3%), camphor (15.6%), b-pinene (5.0%), (E)-methyl
cinnamate (4.6%), bornyl acetate (4.3%) and guaiol
3 Indian Institute of Spice Research
(3.5%). The stem essential oil contains 1,8-cineole
Marikunnu, Calicut, Kerala 673 012, India (31.1%), camphor (11.0%), (E)-methyl cinnamate (7.4%),
guaiol (4.9%), bornyl acetate (3.6%), b-pinene (3.3%) and
a-terpineol (3.3%). 1,8-cineole (28.4%), a-fenchyl acetate
(18.4%), camphor (7.7%), (E)-methyl cinnamate (4.2%)
and guaiol (3.3%) are the main constituents of the rhizome essential oil. The root essential oil contains a-fenchyl
acetate (40.9%), 1,8-cineole (9.4%), borneol (6.3%), bornyl
acetate (5.4%) and elemol (3.1%).
In addition, biological and aroma effects of the main and
minor compounds of the four essential oils of Alpinia galanga are discussed in terms of their possible use in medicine, cosmetics and foods.
Received November 29, 2002
Accepted April 1, 2003

Keywords: Alpinia galanga (Zingiberaceae), essential oils,


leaf, stem, roots, GC, GC-MS

The genus Alpinia belongs to the family Zingiberaceae with Alpinia galanga Willd.
syn. Languas galanga Stunz (greater galangal) and Alpinia officinarum Hance syn. Languas
officinarum Hance (lesser galangal) as the most important species (113). Since A. officinarum is mainly known in Asia (China, India, Indonesia, Japan, Malaysia and Thailand),
but also in Europe, as a drug prepared from the rhizomes and roots and used as tea or

* Correspondence, e-mail: leopold.jirovetz@univie.ac.at

73

L. Jirovetz et al.: Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from
southern India, Acta Pharm. 53 (2003) 7381.

tincture with spasmolytic, antiphlogistic and antibacterial effects, also used as stomachicum and against gastric diseases (4, 5, 7), A. galanga is an essential spice and food flavoring product as well as a medicament or part of medicaments in Asian folk medicine for
various applications, such as against rheumatic oilments, for the treatment of respiratory diseases, as aromaticum and tonicum, but also as aphrodisiacum (2, 3, 813).
Intending to analyse the composition and aroma of the essential oils of plants or
plant parts from southern India that are used in local foodstuffs or in Indian folk medicine, the aim of this work was to identify the constituents of the essential A. galanga oils
from the Kerala area to get information about the volatiles responsible for the above
mentioned applications. Only few papers report the essential oil components of Alpinia
galanga samples from e.g. India (Bangalore, Hyderabad and Himalaya area), Indonesia,
Malaysia and Thailand (2, 3, 811, 13). To the best of our knowledge, no information is
available about the composition of the essential oil of greater galangal from the Kerala
area and its constituents with possible effects useful for food and cosmetic products or
medicinal applications.
EXPERIMENTAL

Plant material
The taxon of the plant of Alpinia galanga was identified by Dr. A. K. Pradeep (Department of Botany, Calicut University, Kerala, India) and a voucher specimen was deposited in the Herbarium of Calicut University. Fresh leaves, stems, rhizomes and roots
of Alpinia galanga were collected in the area of the research farm of the Indian Institute of
Spice Research in Calicut (July 2000), chopped into small pieces and the essential oils
from some hundred grams of leaves, stems, rhizomes and roots were obtained by steam-distillation for 3 hours. The essential oils were dissolved in diethyl ether (pro analysi),
dried over anhydrous sodium sulphate and the solvent was removed by evaporation
(the yields were 0.09% for the leaf oil, 0.1% for the stem oil, 0.23% for the rhizome oil
and 0.08% for the root oil).

Olfactoric evaluation
The essential oils were placed on a commercial odor strip (Dragoco Co., Austria)
and olfactorically evaluated by professional perfumers.

GC and GC-MS
The GC analyses of the essential oils were performed using a GC-14A with FID connected with a C-R6A-Chromatopac integrator (Shimadzu Co., Japan) and a GC-3700
with FID (Varian Co., Germany) connected with a C-R1B-Chromatopac integrator (Shimadzu). The carrier gas was hydrogen, injector temperature was 250 C, detector temperature was 320 C, temperature program 40 C for 5 min to 280 C for 5 min with a
heating rate of 6 C min1. The columns were 30 m 0.32 mm bonded FSOT-RSL-200
fused silica with the film thickness of 0.25 mm (Biorad Co., Germany) and a 30 m 0.32
mm bonded Stabilwax with the film thickness of 0.50 mm (Restek Co., USA). Quantifica74

L. Jirovetz et al.: Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from
southern India, Acta Pharm. 53 (2003) 7381.

tion was achieved using peak area calculations. Some compounds were identified using
retention time correlations with data published elsewhere (1418).
For GC-MS measurements, a GC-17A with a QP5000 (Shimadzu) and a Compaq-ProLinea data system (class5k-software), a GC-HP5890 with a HP5970-MSD (Hewlett-Packard Co., USA) and ChemStation software on a Pentium PC (Bhm Co., Austria)
and a GCQ (Finnigan-Spectronex Co., Germany-USA) with the Gateway-2000-PS75 data
system (Siemens-Nixdorf Co., Germany; GCQ-software) were used. The carrier gas was
helium, injector temperature was 250 C, interface heating was 300 C, ion-source heating 200 C, EI-mode was 70 eV, scan-range was 41450 amu with the cycle time of 0.65 s.
For other parameters, see the description of GC-FID above. Mass spectra correlations
were done using Wiley, NBS, NIST or our own libraries on-line as well as mass spectra
databases published elsewhere (15, 1921).

RESULTS AND DISCUSSION

The odor of the essential oils of Alpinia galanga from southern India was described
as follows: leaf oil: strong Eucalyptus, pinene and camphor notes with herbal side notes;
stem oil: strong Eucalyptus, camphor and pinene notes with herbal side notes; rhizome
oil: strong Eucalyptus and camphor notes with intense fresh-spicy-herbal side notes; root
oil: strong fresh-spicy with camphoraceous, eucalyptol and borneol notes.
Using gas chromatographic-spectroscopic systems (GC-FID and GC-MS) with different types of columns, more than 115 compounds could be identified, among which
mono- and sesquiterpene and cinnamate derivatives were the dominant ones. The main
compounds (concentrations higher than 3%, calculated as percent obtained by GC-FID
on a FSOT-RSL column) determined in the A. galanga leaf oil were 1,8-cineole (28.3%),
camphor (15.6%), b-pinene (5.0%), (E)-methyl cinnamate (4.6%), bornyl acetate (4.3%) and
guaiol (3.5%). The stem oil contained 1,8-cineole (31.1%), camphor (11.0%), (E)-methyl
cinnamate (7.4%), guaiol (4.9%), bornyl acetate (3.6%), b-pinene (3.3%) and a-terpineol
(3.3%) as important constituents, whereas 1,8-cineole (28.4%), a-fenchyl acetate (18.3%),
camphor (7.7%), (E)-methyl cinamate (4.2%) and guaiol (3.3%) were found in the rhizome oil. a-Fenchyl acetate (40.9%), 1,8-cineole (9.4%), borneol (6.3%), bornyl acetate (5.4%)
and elemol (3.1%) were the main compounds in the root oil (see Table I).
Correlations of the described aroma attributes and thresholds of the identified volatiles (2226) with the odor impression of the essential Alpinia galanga oil point to the
following conclusion: the Eucalyptus odor notes can be attributed to 1,8-cineole, camphor/camphoraceous/borneol notes are typical of camphor, camphene, borneol and bornyl acetate, (E)-methyl cinnamate possesses a herbal note and fresh-spicy notes are characteristic of a-fenchyl acetate, elemol and guaiol. Further minor compounds show only
synergistic effects on the described aroma of each essential A. galanga oil, but do not develop additional odor directions.
The above composition of the four essential oils of greater galangal from southern
India with characteristic odor impressions, suggests the use of these essential A. galanga
oils in the flavoring of food products, where fresh (direction of Eucalyptus and camphor)
aromas are required, such as chewing gums and sweets.
75

L. Jirovetz et al.: Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from
southern India, Acta Pharm. 53 (2003) 7381.

Table I. Essential oils of the leaves (L), stems (S), rhizomes (RH) and roots (RO) of Alpinia galanga
from southern India
Componenta
Ethyl acetate
(E)-2-Hexenal
(E)-2-Hexenol
Hexanol
Methyl isobutyl ketone
a-Thujene
Tricyclene
a-Pinene
Fenchene
Camphene
1-Octen-3-ol
Sabinene
b-Pinene
Myrcene
a-Phellandrene
d-3-Carene
a-Terpinene
p-Cymene
Limonene
1,8-Cineole
b-Phellandrene
Benzyl alcohol
(Z)-b-Ocimene
(E)-b-Ocimene
g-Terpinene
trans-Sabinene hydrate
cis-Linalool oxide
trans-Linalool oxide
Fenchone
a-p-Dimethyl styrene
Terpinolene
Linalool
cis-Sabinene hydrate
a-Fenchol
Phenylethyl alcohol
b-Fenchol
Nonanal
cis-p-Menth-2-en-1-ol
b-Thujone
Camphor
trans-Pinocarveol
76

KIb
592
829
852
857
890
927
929
937
943
950
964
973
981
988
999
1010
1015
1019
1025
1029
1032
1034
1037
1039
1055
1060
1065
1075
1080
1082
1084
1090
1092
1100
1104
1108
1111
1113
1115
1125
1131

Lc
ndd
0.12
0.18
0.01
tr
0.04
0.05
1.00
0.17
2.75
nd
0.67
4.97
0.40
0.15
0.41
nd
0.72
0.05
28.34
tr
nd
tr
0.03
0.08
0.26
0.17
0.09
0.07
tr
tr
0.15
tr
0.37
tr
0.04
nd
tr
0.01
15.59
3.37

Sc

RHc

ROc

0.02
0.09
0.03
0.14
nd
0.02
tr
0.47
tr
1.61
nd
0.03
3.29
0.58
tr
nd
tr
0.47
0.06
31.12
nd
nd
tr
0.02
0.05
0.07
0.18
tr
0.05
tr
nd
0.25
tr
0.32
tr
0.02
nd
tr
0.03
11.01
2.26

tre

0.01
nd
tr
0.02
nd
nd
0.04
0.46
0.05
2.43
0.03
0.05
0.09
1.80
tr
nd
nd
1.11
0.78
9.44
tr
0.01
tr
0.03
0.03
tr
0.11
0.04
0.53
tr
0.02
0.39
nd
2.80
nd
0.16
0.01
0.02
0.04
1.24
0.10

nd
nd
tr
nd
nd
0.06
0.55
0.31
2.55
0.02
tr
1.02
0.41
nd
nd
tr
0.61
0.14
28.42
tr
0.02
tr
0.02
0.02
0.04
0.19
0.07
1.16
tr
0.01
0.22
0.01
2.21
nd
0.13
0.05
0.01
0.01
7.71
0.98

L. Jirovetz et al.: Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from
southern India, Acta Pharm. 53 (2003) 7381.

Table I (continued)
Componenta
b-Terpineol
Isoborneol
Isopulegol
Borneol
p-Cymen-8-ol
Terpinen-4-ol
a-Terpineol
Myrtenal
Verbenone
trans-Carveol
a-Fenchyl acetate
cis-Carveol
Carvone
Pulegone
Geraniol
Linalyl acetate
Isopulegyl acetate
cis-Sabinyl acetate
2-Hydroxy-1,8-cineole
Isobornyl acetate
Bornyl acetate
Terpinen-4-yl acetate
Myrtenol
Pinocarvone
(Z)-Methyl cinnamate
Eugenol
(E)-Methyl cinnamate
a-Cubebene
a-Copaene
b-Patchoulene
b-Bourbonene
b-Elemene
a-Gurjunene
b-Caryophyllene
b-Gurjunene
a-Bergamotene
(Z)-b-Farnesene
(E)-b-Farnesene
a-Guaiene
Alloaromadendrene
a-Humulene
Germacrene D

KIb
1135
1141
1145
1154
1167
1175
1182
1184
1186
1208
1210
1214
1228
1230
1242
1249
1251
1262
1267
1274
1277
1281
1283
1307
1320
1335
1352
1360
1378
1383
1386
1399
1405
1432
1434
1437
1448
1451
1454
1461
1465
1469

Lc

Sc

RHc

ROc

0.02
0.09
tr
1.04
0.54
1.39
0.74
2.18
0.20
0.46
0.24
0.22
0.77
0.03
0.13
0.07
tr
0.01
0.42
0.31
4.28
0.11
2.05
0.78
0.85
0.19
4.63
tr
1.07
0.73
0.07
1.57
0.48
1.52
tr
tr
0.14
tr
tr
tr
tr
0.33

0.01
0.15
0.03
1.07
0.61
0.66
3.26
1.76
0.43
0.41
0.26
0.13
0.70
0.04
0.06
0.02
tr
tr
1.35
0.12
3.63
0.30
1.53
0.82
0.32
0.11
7.44
0.05
1.02
0.66
0.14
1.69
0.43
1.66
0.12
tr
0.05
tr
tr
tr
tr
0.16

tr
0.22
0.08
2.48
0.52
0.91
2.58
0.83
0.56
0.33
18.38
0.07
0.89
0.01
0.08
0.03
nd
tr
1.31
0.09
1.67
0.11
0.67
0.91
0.13
0.05
4.22
0.04
0.85
0.51
0.33
0.71
0.29
0.62
0.04
0.09
0.09
nd
0.06
tr
0.07
0.16

tr
0.21
0.11
6.29
0.43
1.25
0.77
0.12
0.06
0.26
40.88
0.22
0.42
0.06
0.02
0.05
0.05
0.05
0.63
0.22
5.35
0.08
0.94
0.12
0.13
0.01
0.30
tr
0.74
0.16
0.21
0.15
0.24
0.83
0.07
0.08
0.01
tr
tr
0.08
0.09
0.32

77

L. Jirovetz et al.: Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from
southern India, Acta Pharm. 53 (2003) 7381.

Table I (continued)
Componenta
Ar-Curcumene
b-Selinene
Viridiflorene
g-Muurolene
Valencene
a-Muurolene
a-Selinene
g-Elemene
b-Bisabolene
g-Cadinene
d-Cadinene
Elemol
(E)-Nerolidol
b-Chamigrene
Carotol
Spathulenol
Caryophyllene oxide
Globulol
Ledol
Viridiflorol
Cubenol
Guaiol
g-Eudesmol
t-Cadinol
t-Muurolol
a-Cadinol
b-Eudesmol
a-Bisabolol
b-Bisabolol
a-Eudesmol
(Z)-a-Bergamotol
(Z,E)-Farnesol
(E,E)-Farnesol
Nootketone
a

KIb
1471
1477
1481
1484
1486
1488
1491
1497
1499
1506
1515
1538
1543
1549
1552
1562
1578
1588
1592
1596
1602
1605
1611
1624
1635
1641
1644
1655
1667
1669
1692
1697
1711
1802

Lc

Sc

RHc

ROc

tr
nd
0.12
0.09
0.01
nd
nd
tr
0.03
0.58
0.16
1.21
0.24
0.12
1.17
0.30
0.26
0.29
0.06
0.15
0.36
3.49
0.31
0.19
0.07
0.06
0.55
0.46
0.10
0.22
tr
0.29
0.11
0.67

nd
nd
0.02
0.01
0.01
tr
nd
tr
0.02
0.74
0.22
1.94
0.33
0.30
2.84
0.11
0.15
0.24
0.09
0.24
0.81
4.87
0.14
0.31
0.03
0.07
0.43
0.54
0.07
0.06
tr
0.17
0.02
1.35

nd
tr
0.08
0.01
0.02
tr
tr
0.02
0.04
0.37
0.18
1.16
0.28
0.21
1.74
0.35
0.05
0.52
0.15
0.36
0.39
3.27
0.05
0.18
0.02
0.14
0.47
0.14
0.01
0.08
0.06
0.07
tr
0.85

nd
nd
tr
0.53
1.07
tr
tr
0.08
0.03
0.44
0.51
3.08
0.42
0.25
2.64
1.07
0.13
0.31
0.43
0.49
0.67
1.16
0.09
0.17
0.15
0.08
0.59
0.26
0.16
0.20
tr
0.05
0.07
0.40

Identification on an apolar FSOT-RSL column.


Kovats index using an apolar FSOT-RSL column.
Concentration calculated as %-peak area obtained by GC-FID analyses.
d nd not detected.
e tr trace compounds (concentration less than 0.01%).
b
c

78

L. Jirovetz et al.: Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from
southern India, Acta Pharm. 53 (2003) 7381.

In cosmetics, these aroma systems may be of interest for e.g. shower gels, soaps,
shampoos and bath products with a fresh top odor.
Medicinal application of essential oils of Alpinia galanga from southern India seems
to be of special interest in two cases (2734): (i) external treatment of rheumatic pain zones using these oils in creams or pastes will be effective due to the relatively high content of camphor and camphene, which are known for increasing the blood supply of these
zones and therefore anti-inflammatory activities, (ii) inhalation of the oils when suffering from respiratory diseases will furnish positive effects because of the high content of
1,8-cineole and fenchol derivatives with known antiphlogistic, antibacterial and cooling
activities.

CONCLUSIONS

As a result of this comparative investigation of different essential oils (leaves, stems,


rhizomes and roots) of Alpinia galanga from southern India, it was found that the composition of these oils differed significantly only in quantity, but not in quality. For the first
time, more than 115 volatiles of the essential oils from Indian greater galangal were
identified. These essential A. galanga oils are rich in mono- and sesquiterpenes as well as
phenylpropane derivatives. The above mentioned main compounds are also responsible
for the characteristic fresh-camphoraceous aroma with herbal and spicy side notes, while the minor components contribute only in a synergistic way. As possible uses of the
greater galangal oils from the Kerala area, applications in food flavoring, in cosmetic
products (for body care) and in medicaments (treatment of rheumatic diseases and as inhalation agents against respiratory troubles) are proposed.
Acknowledgements. We acknowledge the olfactoric evaluations by Mr. Volker Hausmann and
Mr. Wolfgang Hppner, chief perfumers of Dragoco Co., Vienna, Austria, and the correspondence
with Dr. Horst Surburg, Haarmann & Reimer Co., Holzminden, Germany.

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L. Jirovetz et al.: Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from
southern India, Acta Pharm. 53 (2003) 7381.

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S A @ E TA K

Analiza eteri~nog ulja iz listova, stabljike, rizoma i korijena biljke


Alpinia galanga iz ju`ne Indije
LEOPOLD JIROVETZ, GERHARD BUCHBAUER, MOHAMED POTTACHOLA SHAFI i NEETTIYATH KALATHIL LEELA

Istra`ivano je eteri~no ulje listova, stabljike, rizoma i korijena biljke Alpinia galanga
iz ju`ne Indije GC-FID, GC-MS i olfaktometrijom. U sva ~etiri uzorka identificirani su
mono- i seskviterpeni te (E)-metil-cinamat. Ti spojevi su odgovorni za karakteristi~ni miris te upotrebu u narodnoj medicini i prehrani.
Eteri~no ulje listova A. galanga sadr`i 1,8-cineol (28,3%), kamfor (15,6%), b-pinen
(5,0%), (E)-metil-cinamat (4,6%), bornil-acetat (4,3%) i gvajol (3,5%). Ulje iz stabljike sadr`i 1,8-cineol (31,1%), kamfor (11,0%), (E)-metil-cinamat (7,4%), gvajol (4,9%), bornilacetat (3,6%), b-pinen (3,3%) i a-terpineol (3,3%). 1,8-Cineol (28,4%), a-fencil-acetat
(18,4%), kamfor (7.7%), (E)-metil-cinamat (4,2%) i gvajol (3,3%) glavni su sastojci ulja iz
rizoma. Eteri~no ulje korijena sastoji se od a-fencil-acetata (40,9%), 1,8-cineola (9,4%),
borneola (6,3%), bornil-acetata (5,4%) i elemola (3,1%). U radu se diskutira o mogu}oj
primjeni eteri~nog ulja biljke Alpinia galanga u medicini, kozmetici i prehrani.
Klju~ne rije~i: Alpinia galanga (Zingiberaceae), eteri~na ulja, list, stabljika, korijen, GC, GC-MS
Institute of Pharmaceutical Chemistry, University of Vienna, A-1090 Vienna, Austria
Department of Chemistry, Calicut University, Kerala 673 635, India
Indian Institute of Spice Research, Marikunnu, Calicut, Kerala 673 012, India

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